Sissy Shemale Videos » 33

xHamster

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KeekAss

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aShemaleTube

Mistress Strap-on Fucking Her Femboy

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xHamster

2025 Sissy Compilation

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KeekAss

Duda Bunduda Cdzinha sitting prancing on the stool

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ShemaleMovie

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KeekAss

Amazing Blonde Sucking And Fucking In The Livingroom

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JizzBunker

Grindr Sissy SissyWave Brainwash Sissy Captions Feminization

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aShemaleTube

Pink haired sissy gets pegged intensely by her mistress

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aShemaleTube

Exposed sheplacement Sissy Bitch Sucking Daddy Dick

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xHamster

Trixy Hardcore Fucked by Her Boyfriend

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xHamster

He fucks me a nice guy who is very hot

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xHamster

Sissy and Obedient and Sucks It with Pleasure

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aShemaleTube

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Categories: cage, crossdressing, dick, femboy, hd, homevideo, sissy, small cock, uniform

xHamster

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xHamster

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KeekAss

Sissy Transgender princess Rileydix makes you JIZM!

Categories: amateur, ass, big ass, crossdressing, dirty talk, fat, fingering, hd, homevideo, lingerie

KeekAss

Ass-Fuck instructing

Categories: amateur, anal, ass, assfucking, big ass, crossdressing, fat, femdom, feminization, hd

KeekAss

Halloween EP20 Dark princess smoke dance

Categories: amateur, asian, ass, beauty, crossdressing, femboy, halloween, ladyboy, lingerie, panties

xHamster

Dirty slut fucked in reverse cowgirl until he filled up her slutty pussy

Categories: amateur, anal, barebacking, big ass, big cock, colombian, cowgirl, crossdressing, dirty, hardcore

xHamster

Sex Machine Fucks Sexy Crossdresser

Categories: amateur, american, anal, beauty, crossdressing, cum, femboy, feminization, fetish, hd

aShemaleTube

You Are A Fleshlight - Sissy Hypno Video

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aShemaleTube

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aShemaleTube

cute little sissy girl, sensually horny and very adorable

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aShemaleTube

Massaging my sissy clit and cumming like a good sissy

Categories: amateur, blonde, clit, crossdressing, cum, cumshot, femboy, hd, ladyboy, lingerie

xHamster

Sexyfilomena Feel Horny

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aShemaleTube

I Hope Someone Saw Me

Categories: big ass, big cock, exhibitionist, fetish, hd, lingerie, masturbation, outdoor, sissy, slut

xHamster

Secretdreamsfuta Hot Intense Sexual Threesome Tasty Pleasure Sweet Hot Big Ass Swallowing Huge Monster Cock Tasty Hardcore Sex

Categories: 3some, amateur, american, asian, big ass, big cock, crossdressing, cum, cum swallowing, hardcore

xHamster

Feet - Amazing Ass Tranny MILF Fucking Her Ass

Categories: amateur, amazing, anal, ass, assfucking, big ass, dildo, feet, fetish, hd

ShemaleZ

Fucking My Sissy Big Ass With Huge Dildos And A Fuck Machine

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aShemaleTube

Red curly hair shemale jerking on cam

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TrannyOne

Crossdresser hubby fucked

Categories: crossdressing, husband, queen, sissy

xHamster

soaking my stockings and go around with hard cock

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xHamster

peeing all over myself in the tub

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aShemaleTube

leather crossdresser pleases daddy

Categories: amateur, barebacking, crossdressing, daddies, hd, leather, lingerie, sissy

xHamster

Fuck gusto ni Reyna ng kalaswaan yung maraming lalaki na nakapalibot sa kanya

Categories: amateur, asian, beauty, big cock, blonde, cum, filipina, hd, ladyboy, latex

aShemaleTube

Compilation cartoon

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xHamster

Smooth amateur sissy femboy wearing glasses rubs her little clitty to a cummie

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KeekAss

rosy sissy sonya in v-card frolicking with large ass buttplug

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aShemaleTube

Sissy Trainer Aubrey Kate

Categories: compilation, hd, pornstar, sissy

Pornstars: Aubrey Kate

KeekAss

Ultra Sissy Maker four

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aShemaleTube

Horny In Sports bra

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aShemaleTube

Muscle TS babe anal workout pt 1🍑

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aShemaleTube

CUMSHOT UGLY CROSSDRESSER

Categories: amateur, big cock, crossdressing, cumshot, hd, lingerie, masturbation, mature, sissy, small cock

aShemaleTube

Tranny smoking and let's you look up her dress

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xHamster

Your ladyboy neighbour jerking off

Categories: amateur, beauty, big cock, colombian, crossdressing, cum, handjob, hd, jerking, ladyboy

aShemaleTube

Date Night with Mature Crossdresser

Categories: anal, barebacking, blonde, blowjob, couple, crossdressing, cumshot, hd, high heels, lingerie

aShemaleTube

Shemale domina pissing and humilates her sissy bf

Categories: amateur, boyfriend, domination, dominatrix, fetish, humiliation, masturbation, pissing, sissy

xHamster

Lund wali ladki part 2

Categories: amateur, big black cock, big cock, black, chubby, crossdressing, cumshot, desi, fantasy, fat

xHamster

DeeDeeSlut69 Deepthroat and Cum

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aShemaleTube

Exposed Sissy Jake aka Jessi Lynn - Male Dirty Talk Small Penis Humiliation SPH Female Voice

Categories: amateur, crossdressing, dick, dirty talk, femboy, homevideo, humiliation, masturbation, sissy, solo

aShemaleTube

Dana cumming .. wearing her lovely Girly dress

Categories: amateur, crossdressing, cum, dress, hd, homevideo, masturbation, mature, sissy, slut

KeekAss

Naughty sissy attempts to do well, but sans success, not a droplet :) 1/2

Categories: amateur, anal, anal toying, crossdressing, feminization, fetish, hd, masturbation, naughty, pornstar

Pornstars: Lystra

aShemaleTube

Outdoors in a pink camisole and French knickers

Categories: blonde, crossdressing, femboy, french, hd, homevideo, ladyboy, lingerie, outdoor, pov

ShemaleMovie

Gorgeous amateur femboy, stunning trans babe

Categories: amateur, babe, big cock, college, cosplay, crossdressing, cum, femboy, fishnet, gorgeous

AlphaPorno

Thin babes lick each other while they share softcore gems

Categories: anal, babe, bed sex, blowjob, brunette, fake tits, hd, kissing, legs, licking

KeekAss

Trampy Dominatrix OPENS UP SISSY'S TAUT RUMP

Categories: amateur, anal, big tits, couple, domination, dominatrix, femboy, femdom, fetish, hardcore

xHamster

Trans girl Emma

Categories: amateur, british, cumshot, escort, hd, homevideo, sissy, stockings, transsexual

xHamster

Beautiful cute legs

Categories: beauty, cute, feet, fetish, hd, homevideo, legs, pov, sissy, solo

aShemaleTube

Asian sissy faggot grinds on a dildo

Categories: amateur, anal, asian, chinese, crossdressing, dildo, femboy, hd, lingerie, masturbation

aShemaleTube

Dancing for Daddies

Categories: amateur, daddies, dancing, hd, sissy, webcam

KeekAss

Poppers and Spunk PMV

Categories: anal, big tits, bisexual, blonde, blowjob, brunette, compilation, cum, cumshot, facial

xHamster

YUMMY Natural Boy Boobs Hot Shemale Cute Sexy Big Tits Model Cosplayer Sissy Crossdresser Tranny

Categories: big tits, boy, compilation, crossdressing, cum, cum in mouth, cumshot, cute, hd, ladyboy

aShemaleTube

sexual evolution 03.

Categories: asian, ebony, futanari, gangbang, ladyboy, latina, sissy

TrannyOne

French Cuckold Wife and Lesbian Anal Sissy

Categories: amateur, anal, ass, beurette, big ass, big tits, brunette, couple, crossdressing, cuckold

TrannyOne

Big-boobed shemale rides a dildo until she pours the entire floor with sperm

Categories: amateur, anal, anal toying, babe, big tits, blowjob, cumshot, dildo, facial, sissy

xHamster

Seductive Temptations: Crossdresser Kitty's Sensational Journey of Alluring Elegance!

Categories: amateur, american, bbw, beauty, big ass, blonde, crossdressing, cute, feminization, hd

KeekAss

AB093 Cameraman feminized splashing-pegging Japanese and English subtitles

Categories: amateur, anal, crossdressing, dildo, english, feet, femdom, fetish, footjob, handjob

aShemaleTube

Riding a Big FAT Black Dildo Up The ASS

Categories: anal, ass, balls, black, dildo, fat, hd, riding, sissy, slut

xHamster

Being Fucked Doggystyle by My Neighbor

Categories: amateur, anal, barebacking, beauty, big black cock, couple, crossdressing, doggystyle, femboy, hd

xHamster

I fuck the cute nurse on her desk

Categories: amateur, anal, blowjob, crossdressing, cum, cute, desk, doggystyle, hd, homevideo

KeekAss

Solo Blond Ts Masturbating66

Categories: amateur, anal, beauty, big cock, blonde, crossdressing, homevideo, joi, masturbation, pissing

aShemaleTube

workout 5

Categories: fitness, sissy, workout

xHamster

Big Booty Tgirl GAPING Ass with a HUGE DILDO

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xHamster

Sissy Crossdresser BlowJob Training Amateur Mature Crossdresser

Categories: amateur, blowjob, crossdressing, dildo, english, european, homevideo, mature, sissy, solo

xHamster

Indian Gay Crossdresser XXX Naked in Red Saree Showing Her Bra and Boobs

Categories: bra, crossdressing, gay, hd, homevideo, indian, lingerie, nude, pornstar, sissy

Pornstars: Red XXX

KeekAss

Strength Bottom Damsel Tiffany Ciskiss Pt 1

Categories: amateur, anal, anal toying, ass, blonde, cosplay, crossdressing, dildo, extreme, feet

ShemaleZ

Pegging Ass Of Sissy Slut Bailey Wilde

Categories: amateur, ass, blonde, fetish, hd, lingerie, pegging, sissy, slut, stockings

aShemaleTube

Black robe and fishnet pantyhose

Categories: black, blonde, crossdressing, femboy, fetish, fishnet, hd, ladyboy, lingerie, pantyhose

xHamster

Anal Stretching With Big Balls Popping In & Out Asshole

Categories: amateur, american, anal, anal toying, ass, balls, big cock, cum, cumshot, extreme

xHamster

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8

Categories: amateur, american, anal, bdsm, beauty, big ass, compilation, crossdressing, femboy, hd

aShemaleTube

the goths; Sims Quickie -The Principal 3

Categories: chinese, ebony, fetish, group sex, hd, ladyboy, latex, quickie, sissy

xHamster

Adventures with Me: Exploring Life's Thrills

Categories: american, big ass, big cock, big tits, deep throat, femboy, feminization, hd, homevideo, ladyboy

xHamster

Sexy Omanko Part 5 - Paichan After Class

Categories: amateur, asian, college, cosplay, crossdressing, hd, japanese, sissy, solo

KeekAss

Sissy victim plays with their self

Categories: amateur, brunette, crossdressing, cum, dick, dildo, ebony, hd, homevideo, master

ShemaleZ

Sissy Slut Anal Masturbation With Clit Closed In Chastity Sc.18

Categories: amateur, anal, clit, fetish, hd, masturbation, sissy, slut, solo, stockings

ShemaleMovie

[fr] La chute tk17

Categories: 3d, bdsm, british, domination, sissy, spanking

aShemaleTube

CATALINA - COMPILATION

Categories: amateur, big cock, compilation, hd, latina, masturbation, sissy, solo, tranny, transsexual

aShemaleTube

Orange bra and panties with black hold-up stockings

Categories: big cock, black, blonde, bra, crossdressing, femboy, fetish, hd, ladyboy, lingerie

xHamster

Sissy in chastity show feet and fuck hole

Categories: anal, beauty, big ass, blonde, crossdressing, dildo, feet, femboy, hd, ladyboy

KeekAss

Sissy OClock Brief Jean Cut-offs Smacking Blinking Bulls eye Femboy Striptease Fabulous Brief Cutoffs

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aShemaleTube

Smoking sissy

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aShemaleTube

Pale gorgeous Sissy bred deep by hung BBC

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xHamster

Blond CD tranny with loud moans is pounded hard in mirror by BBC The Pole Invader - Candy Ass Sissy

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Pornstars: Candy Ass

aShemaleTube

Sport sissy have some solo fun after workout in gym with her new tentacle dildo

Categories: anal, asian, big ass, big cock, crossdressing, dildo, femboy, funny, gym, hd

Pornstars: Viper

ShemaleMovie

Alexia St James Farm Boy, Solo and Hairy youthfull stud three Scenes

Categories: anal, babe, blonde, blowjob, boy, caught, crossdressing, hairy, sissy, solo

aShemaleTube

Trap-a-Holic PMV vol.1

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HDSex

I’m Elena Andreou, a wild cross-dressing slut with huge breasts craving a good fucking and climaxing hard

Categories: anal, bbw, close up, crossdressing, cum, cumshot, dildo, fishnet, huge tits, jizz

aShemaleTube

Cojuendo con un macho que conoci en el trabajo

Categories: crossdressing, hd, peruvian, sissy

KeekAss

Sissy mega-bitch Lola busting a big black cock

Categories: amateur, anal, big black cock, big cock, bitch, black, blowjob, crossdressing, femboy, hardcore

aShemaleTube

Sexy Latin tgirl anal edging 💋

Categories: anal, big ass, edging, fishnet, hd, homevideo, latina, lingerie, masturbation, sissy

xHamster

I love fucking Machines 498

Categories: anal, anal toying, ass, big ass, crossdressing, cum, dildo, fucking machine, german, hd

xHamster

Rikki Ocean Lets You Worship Her Cock and Balls on Your Knees

Categories: american, balls, big cock, big tits, cum, cumshot, dick, femboy, hd, knees

xHamster

Fuck me Friday!

Categories: amateur, american, anal, anal toying, crossdressing, cum, cumshot, dick, hd, homevideo

Pornstars: Friday

xHamster

Snow elf with big hard cock making creamy cum

Categories: amateur, beauty, big cock, colombian, creampie, crossdressing, cum, dick, handjob, hd

KeekAss

Peruvian transvestite she-male in white underwear with huge fake penis anal invasion injection

Categories: amateur, anal, ass, bbw, bdsm, big ass, brunette, chubby, crossdressing, dick

ShemaleZ

Sissy Maid Gets Called In To Give Head With Christian Xxx

Categories: big ass, big cock, booty, booty shake, cum in mouth, deep throat, dick, hd, latina, maid

xHamster

Living Sex Doll Bound and Struggling

Categories: amateur, american, bondage, bound, crossdressing, doll, fetish, hd, ladyboy, mask

aShemaleTube

Christmas is Cumming! Are you?

Categories: amateur, blonde, crossdressing, cum, cumshot, hd, homevideo, lingerie, masturbation, sissy

aShemaleTube

Blond sissy bombshell fucked hard and masturbates pov

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aShemaleTube

Sexy Sandy shows off her new dress

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aShemaleTube

TsOmaina hot blonde transgirl fucking the neighbor

Categories: amateur, anal, barebacking, big ass, big cock, blonde, femboy, fetish, hd, ladyboy

xHamster

Smoking hot T-girl Irene Aoki jerking off in sheer black pantyhose

Categories: anal, black, dick, hd, jerking, masturbation, pantyhose, sissy, smoking, solo

KeekAss

Sissy Motel Self Restrain Bondage Joy

Categories: amateur, bdsm, bondage, brunette, crossdressing, fetish, hd, hotel, mature, motel

xHamster

Trans Bailey Wilde Fucks Hot Crossdresser

Categories: amateur, american, anal, beauty, big ass, big cock, crossdressing, cum, feminization, fetish

aShemaleTube

BBC vs Asians Compilation 3

Categories: anal, asian, barebacking, big black cock, big cock, compilation, hd, interracial, ladyboy, sissy

aShemaleTube

Being out for some punishment

Categories: crossdressing, femboy, ladyboy, pantyhose, punishment, sissy, stockings, toys

xHamster

In Louboutin Heels

Categories: amateur, crossdressing, feet, fetish, hd, high heels, italian, ladyboy, mature, pantyhose

aShemaleTube

Nice Cock Splice Vertical Video

Categories: amateur, asian, chinese, crossdressing, dick, femboy, sissy, small tits

TrannyOne

Tears of the Femdom - a Link to the Ass

Categories: amateur, asian, ass, cosplay, cum, cumshot, dick, dirty, fantasy, femdom